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As a young boy, Jenny's original name was John, in honour of her deceased father who drowned at sea while trying to rescue a woman. At an early age, Jenny decided that she wanted to be female. She was able to obtain female hormones at the age of 13, which prevented her from experiencing puberty as a male. John chose the name Jenny to honour her sister, Eugenia, who hosted and aided their family when they moved to Athens.

Jenny went on to complete sex reassignment surgery at the age of 20 becaming one of the top models in Greece. Her high profile brought about scandal and gossip.

During that time she also published her book Οι Άγγελοι Δεν Έχουν Φύλο (The Angels Have No Gender), which was also released as a comic book called JennyX.

A year later, Jenny spoke with reporter Tatiana Stefanidou and complained that Sitians were accusing her of working as a prostitute and organising sexual orgies. They boycotted her restaurant, trying to drive her out of business. Jenny denied doing such things and claimed that the rumours were started out of prejudice; patrons of her cafe complained about even such minor things as the ambient music. Jenny also claimed that many rumours were started by a lesbian student who was attracted to Jenny and who decided to exact her revenge upon discovering that the feeling was not mutual.

Her 1997 affair with District Attorney George Sakelaropoulos, who met her while trying to close her brothel in Rhodes, was quite notable. The affair is the only relationship of Hiloudaki that has been followed closely by the media. Greek society was shocked until the couple broke up and Sakelaropoulos returned to his previous family.

She lives with her 2 cats — a Siamese named Leo, a Turkish Angora named Snow White — and a bird named Kitsos. In her spare time, she enjoys collecting antiques and Swatch watches,